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EPISODE 152: DLT Sales Leader Chris Wilkinson Says Taking This Approach to Your Sales Career is Critical for Your Success
CHRIS’ FINAL TIP TO EMERGING SALES LEADERS: “Every day is a chance for a new beginning – embrace that opportunity. Focus on what you can control, influence what you can influence and smile otherwise.”
Prior to coming to DLT, he held sales leadership positions at immixGroup and DHL.
Find Chris on LinkedIn!
Fred Diamond: Why don’t you tell us a something about you that we need to know?
Chris Wilkinson: Thanks, Fred. One of the things I’d like to communicate in the Game Changers podcast today is really around ownership and accountability. I very much view salespeople as a business owner, sales clearly being one of the most important pieces of building a business. Again, I feel like I’ve been privileged to have some tremendous opportunities in my career and some exposure to some tremendous training. I really appreciate being here today.
Fred Diamond: Tell us a little bit about DLT. Tell us what you sell today and tell us what excites you about that.
Chris Wilkinson: We sell a suite of services that accelerate public sector growth for technology companies, and as a solutions aggregator we represent best of breed technologies to three major customers. It’s typically our technology vendors, our value added resellers and solutions providers and then ultimately our joint government customers. A couple of things that really excite me about playing this role in the channel is one, the exposure you’re getting to emerging new technologies and staying ahead of the curve. We’re constantly being introduced to new capabilities that enable our customers to more effectively accomplish their missions.
Then I would say the second piece of it is more dealing with our customers, because we support three different constituents. We represent such a broad spectrum in technology, it’s very rare where we’re involved in a conversation where we can’t find a way to provide our customer some sort of value.
Fred Diamond: Tell us some of the technology vendors that you offer, just to give our listeners listening around the globe a little bit of context.
Chris Wilkinson: We’ve aligned our sales, our marketing and our chief technology office around six technology domains that really align well to the way our customers buy technology, and they typically align well to the way our vendors and our partners are coming to market. Some of our major providers are the Oracles of the world, the AWS’s of the world, the Red Hats of the world and then we’ve got some emerging new capabilities around big data and analytics in the HortonWorks (Cloudera), the cloud area relationships. From a cyber-security perspective, it’s everything from the McAfee’s, the Symantec’s, all the way through to some of the CrowdDtrikes and other emerging capabilities.
Fred Diamond: I want to go back to something you said in the introduction. You said “ownership and accountability.” Talk about that for a little more before we get into some details on the podcast.
Chris Wilkinson: I think as a sales rep you’re so responsible for driving and developing net new business that if you think about your role within that sale cycle as a business owner ensuring the success of both your organization and your customer, I think it makes the perseverance required to be a sales rep much more palatable.
Fred Diamond: What does that mean, what does that look like? We have Sales Game Changers listening around the globe. What should I be thinking about? I love the idea that you’re talking about here and we’ve had that concept numerous times on the Sales Game Changers podcast that at the end of the day, you’re working for yourself. You have to establish your business and you want to be the VP of Chris Wilkinson Industries, if you will and now you’re providing great service to DLT. What does that logistically look like to the people listening on the call today?
Chris Wilkinson: It’s a good question. I would say that it really involves you positioning yourself in such a way that you are interested in ensuring that you’re creating or maximizing the profitability of the business that you’re supporting for your vendor, for your entity that you’re working for. You’re also ensuring that your customer is successful with the implementation of whatever solution that you’re providing to them, striking that balance of profitability ensuring you’re doing the right thing for the business and being fair to your customer to ensure that you’re giving them the right solution to enable their success.
Fred Diamond: How did you first get into sales as a career?
Chris Wilkinson: It’s an interesting story. I studied psychology in college and I had a great psychology professor that pulled me aside after a couple of classes and asked me what I wanted to do after college. He then went into a bit of the economic realities of graduating after a 4 year degree in psychology and suggested that I might want to look at something like sales. I almost immediately transitioned my field of study and my major to business administration and a minor in economics, because I was really looking forward to getting out of college and launching myself into a career really beginning to build my own personal brand.
Fred Diamond: Was DHL the first place you went after college or did you do some other jobs before that?
Chris Wilkinson: Actually, I worked for an entrepreneurship at DMG Securities, I wanted to be a stock broker and that didn’t work out for a number of reasons. I interviewed at a couple of places, I ended up landing at DHL which turned out to be a blessing in disguise. It was a really tough job and it was a challenging sales environment but it was very rewarding and had a tremendous training program that I think I didn’t necessarily appreciate at the time compared to how powerful it really was. It really launched the foundation of my career.
Fred Diamond: Just curiously, in retrospect what were some of those things that you learned there that you’ve employed over the course of your career?
Chris Wilkinson: It was early introduction to authentic selling, being yourself, following a process. It was a very rigid sales process to qualify a prospective customer and then frankly, just getting you out of your comfort zone introducing you to cold conversations on a daily basis.
Fred Diamond: Are you comfortable with that? You’re in a business where you have a whole bunch of inside sales people and they have to make phone calls. How did you get past that?
Chris Wilkinson: I think if you don’t feel the butterflies before your first few calls of the day, I don’t know that you’re doing it right. I played sports and no matter how long I played both in high school and in college, every game you had butterflies. As a sales rep I feel like if you’re not approaching those calls with those same sort of nerves and butterflies in your first few calls, you’re probably not as invested in it as you need to be to be successful.
Fred Diamond: When you have those butterflies and you’re concerned that you may not be ready to go, what are some of the things that you’ve instructed some of the young sales professionals over the years to get past those butterflies?
Chris Wilkinson: Just be themselves and just have a conversation. I think more often than not, as a sales rep you’re inclined to talk more and tell people what you know. I think you really need to focus on listening to your customer, don’t be afraid of silence, let the customer fill the gap, you’d be surprised at what they tell you sometimes when you’re on those first few sales calls and you’re feeling those butterflies. I think you have a tendency as a sales rep to want to fill that silence and limit that discomfort, when if you just give your customer some time to put some thoughts together and speak, you might be surprised at what you learn.
Fred Diamond: That’s very powerful. Let’s talk a little more about you, what are you specifically an expert in? Tell us a little more about your specific area of brilliance.
Chris Wilkinson: I don’t know that I really view myself as an expert, I do know that I’m willing to work very hard. I have found that it seems that I’ve got a skill set to be able to translate complex technological concepts into simplified concepts or into stories that you can tell. To train resources to be able to bridge the gaps between the technical resources within our customer bases that are really performing the services or providing a solution, bridging the gap with the mission owners and the business owners, helping them to communicate more effectively to leverage technologies to ultimately enhance or solve or perform their mission.
Fred Diamond: You’re leading sales here at DLT, again DLT provides solutions working with technology vendors, value added resellers to serve the government customer. You must have had some great mentors along the way, why don’t you tell us about an impactful sales career mentor and how they impacted your career?
Chris Wilkinson: To be honest, Fred, there’s been a lot of folks that have impacted my career at different stages of my development even in different specific skill sets. If you don’t mind, a couple that come to mind, Art Richer here, our CEO at DLT certainly taught me the power in natural charisma, really helped me to hone authentic leadership skills and also really taught me the power of having a thorough business plan to ensure that you’re executing effectively.
Steve Limbert was one of my first managers out of the gate, I’ve got to give him some credit back at ImmixGroup for putting up with me, helping me understand the power of professionalism both internal and external to the office. He also taught me some soft skills, the fact that your soldiers need to eat first and you need to really be about your team enabling them to be successful.
Bill Rucker is another name that has really helped me in different stages of my career, particularly as it relates to exposure to different sales techniques or even different perspectives that you bring to an everyday conversation. I find myself thinking back to a lot of the lessons that he’s taught me as I’ve gone through sales environments.
David Stewart really helped me with consistent sales operations and the need for the consistency in the way that you actually operationally manage your business to be effective, and then lastly I would probably want to give a shout out to Amy Kelly. I think she did a tremendous job at teaching me that having a very powerful peer relationship that could function as a sounding board really enables you to bring new ideas to market much more effectively.
Fred Diamond: Those are some great mentors. The Institute for Excellence in Sales, one of the sponsors of the podcast each year gives out a Lifetime Achievement Award to a high achieving sales leader and Art Richer was the recipient in 2016. Those are some very talented people. Before I ask you about the two biggest challenges you face, I want to go back to the concept of authentic selling. It’s come up a couple of times, you mentioned that Art even helped you understand that, or authentic leadership. Can sales professionals make the shift? And they have to at some point, because you’re right, at the beginning you want to give features, benefits, you have scripts, you don’t want to hear dead silence so you’re trying to do all those things that we just talked about. Does it happen one day, all of a sudden you’re authentic or does it happen over time? Do you remember when you made that shift?
Chris Wilkinson: It happens over time. I don’t know that I can point to a specific instance where a lightbulb went off, I almost wish I could. The reality is as you’re getting exposure in any sales environment, you’re going to be taught Sandler, you’re going to be introduced to a number of different sales concepts that in and of themselves are really tremendously effective at helping you to bring products to market to enhance your own skill sets. I think you need to look at bringing those together with your own personality in order to be effective. It’s very easy when I work with junior sales reps to see them using the same philosophy, the same technique repetitiously.
It’s easy to poke holes at that philosophy and I haven’t seen that to be as successful as leveraging different pieces of each of those different methodologies that are more natural to you, authentic to you. I think over time you start to find a way to be yourself yet employ these different techniques to help you be effective at one, qualifying your prospect, overcoming objectives and morphing to their different personality and their skill set as well. Your customer brings a very critical component to the sales equation in their personality and the way that they need to come to a solution or a conclusion throughout that process. I feel like if you’re forcing methodology onto them and it’s not connecting, you’re not going to be successful. It’s really about bringing those different techniques together with your own personality and your natural charisma.
Fred Diamond: What are the two biggest challenges you face today as a sales leader?
Chris Wilkinson: If I had to limit it to two, I would say time management as it relates to prioritization. Fortunately or unfortunately, there’s no shortage of opportunity in our organization right now but I think in sales in general. It’s very difficult to make sure that you are spending your time in the areas that are going to offer the greatest return on investment for you and for the company in a lot of cases.
I would say the second challenge that I’m having right now that’s very top of mind is staffing resources, particularly leadership resources with the right skill sets, with the right capabilities in the right seats to perform the mission that we’re bringing to market right now. We’re going through some tremendous growth here and we’ve got a number of new opportunities that we need to fill. The reality is there are some folks out there that have been trained at interview very well, it’s almost like you’re getting a different person the first day that they show up on the job sometimes. That’s a challenge that I think that everyone faces pretty regularly, but right now those would be the two that probably jump top to mind.
Fred Diamond: Tell us about your #1 specific sales success or win from your career you’re most proud of, take us back to that moment.
Chris Wilkinson: The guidance is probably debatable, but I’ve enjoyed the career. I’d say it’s a little bit difficult. In our role as a solutions aggregator in the market space there’s a couple of different types of sales. Clearly, it’s exciting for us whenever we’re able to bring our suite of services to bear to a qualified prospect to bring them into our programs. Signing some big name accounts over my past 13 or 14 years or so in the space like Adobe, BMC, Tenable, some of those big companies have been very exciting. Progressing AWS to distribution here at DLT, very exciting.
Then there’s the other side of our business where we work very closely with the demand generators, the demand creators of our technology vendors and our partner ecosystem. There’s been a couple notable wins that come to mind over my career, one would be winning a 5 year IDIQ with a strategic vendor and partner of ours a few years back, winning a 5 years SEWP EWA after our partner at that time had been challenged to do so for at least 6 years in advance, that was a pretty exciting moment for us. I’d say probably the one that stands out the most from that side of our sales success would be winning my first 8-figure deal, those are pretty special deals and that one will always hold a special place.
Fred Diamond: Before we get to a quick message from one of our sponsors, again we’re talking to Chris Wilkinson, Senior VP of Sales at DLT. Chris, did you ever question being in sales? I really like the stuff we’re talking about here as it relates to authentic selling, authentic leadership, ownership and accountability, but sales is hard. Especially to have gotten to the level where you are and the marketplace that you’re competing in is extremely competitive, it’s very difficult. One thing we didn’t talk about is the challenges facing your customer, your government customer. Did you ever question being in sales? Did you ever say to yourself, “It’s too hard, it’s really just not for me”?
Chris Wilkinson: Very early on selling DHL, absolutely, I’d say probably within the first 6 months of that job. If it weren’t for qualifying for advanced basic training that they had and really learning different ways to approach my customer, there were times where I questioned whether it was the right career move for me. It was a challenging environment, so I’d say yes, absolutely, I did experience some time where I wondered if sales was the right thing for me. I think I’m pretty fortunate to have overcome that challenge early on in the career, not to say that you won’t face that challenge again at any point in time, but without a doubt the first 6 months selling DHL was a very difficult time.
Fred Diamond: Chris, what’s the most important thing you want to get across to the junior selling professionals to help them improve their career?
Chris Wilkinson: Hard work ethic is very big with me. I would want to make sure that I talk about the value and just working hard, and outperforming your peers to naturally accelerate within an organization. Be naturally curious, human nature is to be curious and at some point it seems as we go through sales training we begin to lose that and we want to talk and tell as opposed to listen more than we talk. I mean that both with your customers and also with your peers. Be a sponge on both sides of it, from a customer perspective certainly understand what it is they’re really trying to accomplish and help them be successful, and then from a peer perspective you’re always exposed to opportunities to continue to learn as you’re engaging with peers and with mentors.
I’m a big subscriber to the “as one more question philosophy.” When you’re uncomfortable and you think you’ve asked all the question you can ask, push yourself to ask one more question. We’ve talked about it throughout the podcast today, but be authentic, that’s another piece that I think is critical. If you don’t believe in what you’re selling, if you’re not passionate about what you’re selling and if you’re not being yourself, it’s probably going to be difficult to be successful.
Fred Diamond: What do you do when you see sales reps who don’t have the passion that you have?
Chris Wilkinson: There are certain things that you can do to try and train because I think sometimes to get the passion out of them, they need to believe that they can be successful. If you can help them through techniques to find their first few successes, I’ve seen that passion will naturally present itself. In other cases, to be honest with you, we’ve helped some sales folks by demonstrating that this might not be the right field for them. I like to joke that I’m a simple guy so I think in simple terms. If you put me in scrubs, I’m just not going to be a doctor and the same can be true for some sales folks.
Fred Diamond: What are some of the habits that you historically have put into play to ensure your success?
Chris Wilkinson: I learned very early on one of the habits that’s been very powerful for me is not being afraid of silence. Again, I mentioned a couple of minutes ago in the podcast here that it is human nature to fill the silence in a natural conversation. When you’re selling, you’re even more eager to fill that silence because it becomes even more uncomfortable, I’m very mindful to not fear that silence. One of the other things that I’ve embraced early on is sales is a number’s game and we have the ability in sales to measure key performance metrics certainly around effort and certainly around results as well. I learned very early on that I was going to work harder than the person next to me and I was not going to allow them to beat me in the metrics that measured effort. I may not always win in result, but I wasn’t going to be beaten in effort and if I was, you were going to have to work really hard to do that. I think that was very powerful early on in my career, especially when I think I was closing deals in brute force more than finesse.
Fred Diamond: Tell us about a major initiative you’re working on today to ensure your continued success.
Chris Wilkinson: Personally, it’s a commitment to ongoing education and self-improvement, a big initiative for me. Then I’d say professionally it’s a mental commitment to innovation and constantly evaluating what could we be doing new in our business to provide more value to our customers.
Fred Diamond: Again, we’ve talked about the fact that you’re in a very challenging marketplace, we talked about some of the challenges of finding great sales leaders, and sales is hard. To be at the highest level of sales especially in the marketplace that you’re competing in, people don’t return your phone calls, there’s a mackerel of things. The marketplace that you worked for shut down at one point in the not too distant past, if you will, but why have you continued in sales? What is it about sales as a career that has kept you going?
Chris Wilkinson: I’ve eluded to it earlier, I see myself as a business owner and I’m driven to build the best business that we can possibly build for myself, for the people around me and ultimately for my customers as well. I think that feeling of ownership and accountability makes it easier to be persistent and makes it easier to not get to high with the highs and not get too low with the lows. I’d say that’s probably a big piece of it.
Fred Diamond: That’s a pretty big message there, the whole concept of business ownership and a lot of the stuff we’ve talked about today. I think you really do need to believe in what you’re selling, you need to believe in the mission of your customer. We haven’t really talked about that too much, but to hit the highest level of sales, you really need to have that. I love the concept, the through line that we’ve had on today’s podcast is authentic leadership and how you as a sales professional listening to the podcast can be as authentic as possible. Chris Wilkinson, you’ve given us some great insights today, you’ve given us a lot of great ideas, I want to thank you for being on the podcast. We have Sales Game Changers listening around the globe to this podcast, why don’t you give us one final thought to inspire them today?
Chris Wilkinson: A cliché comes to mind immediately: every day is a chance for a new beginning. I would say embrace that opportunity, focus on what you can control, influence what you can influence and smile otherwise. I’d say find something that you can believe in and that you can be passionate about, believe in yourself. Embrace development opportunities, they really are all around you. The other thing is be proactive, it’s so easy in any career to be reactive to just the day to day things that are thrown at you in business. Making time to be proactive is critical to be successful in sales.
Fred Diamond: Mental commitment to innovation. Good for you, very good stuff.